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Substituted 2,3,4,5-tetrahydro-1h-pyrido[4,3-b]indoles, methods for use thereof

a technology of tetrahydropyrido[4,3-b]indoles and substituted 2,3,4,5-tetrahydro1hpyrido4, 3bindoles, applied in the directions of drug compositions, metabolism disorders, organic chemistry, etc., can solve the problem that the effect of reducing the concentration of calcium cytosolic concentration of calcium homeostsis modulators cannot be achieved, and achieves the effect of not inducing undesirable effects

Inactive Publication Date: 2019-08-01
IVACHTCHENKO ALEXANDRE VASILIEVICH +2
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  • Summary
  • Abstract
  • Description
  • Claims
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Benefits of technology

The text is about a method called "focal library" that helps researchers create specific libraries of compounds to find new drugs or improve their properties. This technique is particularly useful when trying to target specific proteins or receptors in the body. The goal is to increase the chances of finding promising new molecules and minimize the time and resources needed for optimization.

Problems solved by technology

Nearly all mentioned drugs prevent the penetration of calcium ions into cells, however, calcium homeostsis modulators capable for effective reducing of calcium cytosolic concentration which became elevated as a result of some pathologic processes have not been known yet

Method used

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  • Substituted 2,3,4,5-tetrahydro-1h-pyrido[4,3-b]indoles, methods for use thereof
  • Substituted 2,3,4,5-tetrahydro-1h-pyrido[4,3-b]indoles, methods for use thereof
  • Substituted 2,3,4,5-tetrahydro-1h-pyrido[4,3-b]indoles, methods for use thereof

Examples

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example 2

General Method for Preparation of 5-[2-aryl(or azaheterocyclyl)ethyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoles of the General Formula 1.2

[0250]A. 200 mg of PtO2 is added to a solution of 2 mmol of 5-[2-aryl(or azaheterocyclypethenyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole of the general formula 1.1 in 40 ml of ethanol and the resultant mixture is hydrogenated by hydrogen at stirring and room temperature for 24 hs. Upon completion of the reaction (LCMS monitoring) the mixture is filtered or centrifugated. Filtrate is evaporated in vacuo, and the residue is purified by chromatography on silica gel impregnated with triethylamine eluting with CHCl3-hexane-Et3N mixture (3:6:1) or recrystallized from the proper solvent. 5-[2-Aryl(or azaheterocyclyl)ethyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoles of the general formular 1.2 are prepared.

[0251]B. A solution of 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole 2 (7,5 mmol), 7,5 mmol of tetramethylguanidine and 15.0 mmol of aryl(or azaheterocy...

example 3

General Method for Preparation of 5[2-aryl(or azaheterocyclyl)ethynyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoles of the General Formula 1.3

[0252]50 mg (0.2 mmol) of CuSO4×5H2O, 74 mg (0.4 mmol) of 1,10-phenanthroline, 890 mg of dry powdered K3PO4 and 2.2 mmol of halogenacetylene 5 is added to a solution of 2 mmol of, 3,4,5-tetrahydro-1H-pyrido[4,3-b]indole 2 in 3 ml of toluene under argon atmosphere. The mixture is stirred at temperature 80-85° C. for 12 hr. Monitoring of the reaction was carried out by means of LCMS. Upon completion of the reaction the reaction mixture is diluted with ester and filtered. The solvent is evaporated, the residue is purified by chromatography on silica gel impregnated with triethylamine eluting with hexane-chloroform-Et3N mixture (6:3:1). 5-[2-Aryl(or azahetero cyclyl)ethynyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b] indole s 1.3 are prepared, among them: 2-methyl-5-p henylethynyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole 1.3(1), LCMS: m / z 287 [M+H], 1E1 N...

example 4

[0253]General method for preparation of 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoles of the general formulas 1.1, 1.2 in the form of salts. To a solution of 1 mmol of 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole of the general formulas 1.1 or 1.2 in ester, dioxane or methanol 0,76 ml (2,1 mmol) of dioxane or methanol solution of HCl or HBr is added. The precipitated white solid is separated, washed with acetone and / or ester, dried in vacuo. It gives 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoles of the general formulas 1.1, 1.2 in the form of salts, among them: cis-2-methyl-5-(2-phenylethenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole hydrochloride 1.1(1)HCl, LCMS: m / z 289 [M+H]; trans-2-methyl-5-(2-phenylethenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole hydrochloride 1.1(2)HCl, LCMS: m / z 289 [M+H]; trans-2-methyl-5-[2-(pyridin-4-yl) ethenyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole hydrochloride 1.1(3)HCl, LCMS: m / z 290 [M+H]; cis-2-methyl-5-[2-(pyridin-3-yl)ethenyl]-2,3,4,5-tetrahydro-1H...

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Abstract

The present invention relates to compound of the formula 1.2, or a pharmaceutically acceptable salt, or hydrate thereofwherein R1 is C1-C5 alkyl;R2, is independently hydrogen, halogen, C1-C3 alkyl, CF3, OCF3 or OCH3; i is 1, 2,3, or 4;Ar is unsubstituted phenyl or substituted phenyl substituted with halogen, C1-C6 alkyl, C1-C6 alkoxy, a substituted amino group or trifluoromethyl; or Ar is a substituted or unsubstituted 6-membered aromatic heterocycle one or, with two nitrogen atoms in the heterocycle;excluding the compounds of the formulas A1-A4The invention relates to the novel chemical compounds, methods for their preparation and use as antagonists of 5-HT6 receptors, simultaneously regulating homeostasis of calcium ions in cells. The invention relates to the novel annelated azaheterocycles—2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoles, to methods for their preparation, to pharmaceutical compositions, including these compounds as active substances, and to methods of treatment and profylaxis of various diseases.

Description

CROSS REFERENCE TO RELATED APPLICATIONS[0001]This application is a Division of application Ser. No. 14 / 791,280, filed Jul. 3, 2015, which is a Division of application Ser. No. 13 / 844,825, filed Mar. 16, 2013, which is a Division of application Ser. No. 12 / 594,453, filed Oct. 2, 2009 which claims benefit of priority to the International application PCT / RU2008 / 000196 filed Apr. 1, 2008, which claims benefit of foreign priority to the Russian Federation application RU 2007112666 of May 4, 2007. The priority applications are hereby incorporated by reference in their entirety.FIELD OF THE INVENTION[0002]The invention relates to the novel chemical compounds, methods for their preparation and use as antagonists of 5-HT6 receptors, simultaneously regulating homeostasis of calcium ions in cells. More specifically, the invention relates to the novel annelated azaheterocycles 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoles, optical and geometrical isomers, racemic mixtures, pharmaceutically accepta...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07D471/04A61P3/14
CPCC07D471/04A61P3/14
Inventor IVACHTCHENKO, ALEXANDRE VASILIEVICHIVASHCHENKO, ANDREY ALEXANDROVICHSAVCHUK, NIKOLAY FILIPPOVICH
Owner IVACHTCHENKO ALEXANDRE VASILIEVICH
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